Favorite Songs By Favorite Artists: Taylor Swift

Over the course of the last decade, no artist has been scrutinized and debated more than Taylor Swift. Large swaths of music fans don’t understand the appeal citing either weak vocals, the fact they’re out of her target demographic, or both in their critiques. But through it all Swift has grown into a one woman machine who’s become the heart and soul of the music industry. The first genuine superstar of the social media age, she connects with fans at a level never before seen. Her impact and influence cannot be understated.

On some level Swift is a brilliant business woman. You don’t sell a million copies of your last three albums – Speak Now (2010), Red (2012) and 1989 (2014) – in the first week by accident. Swift knows her audience inside and out, thus giving them exactly what they want.

I’ve loved Swift ever since “Our Song” was released to country radio in the summer of 2007. Her five albums have constantly been some of my favorite records during the years they were released. In fact, no other artist has gotten me more excited for new product than Swift. Why? Simply put, her songwriting speaks to me. No one crafts lyrics like her, framed impeccably in the melody and instrumentation that best suits the song. Taylor Swift has it all figured out – haters be damned – and is laughing all the way to global domination.

Ranking my 25 favorite songs of hers was a challenge. I finally got it down to list I could live with, which you see here, complete with commentary. These truly are my favorite songs by a favorite artist, a singer who’s grown from a teenager to a fully fledged woman before our eyes.

#25

The Way I Love You

Fearless (2008)

Written By: Taylor Swift & John Rich

I was obsessed with this thumper in the early days of the Fearless era, stomping to the infectious drumbeat and screaming along as she belted the lyrics. Swift rarely expands her co-writing circle, but she let in Rich, if only for a one-off. My ears find this a bit cluttered now, but how I loved it back then.

#24

22

Red (2012)

Written By: Taylor Swift, Max Martin, and Shellback

If ever there was a perfectly optimistic beat driven anthem about the beautiful bond that only exists between friends, it would be this one, hands down. So what gets Swift and her gal pals “feeling like we’re 22?” Well, eating breakfast at midnight, forgetting about deadlines, and dreaming instead of sleeping. What would come off as tepid dreck in anyone else’s grip works perfectly to capture Swift’s wholly imperfect world.

#23

I Knew You Were Trouble.

Red (2012)

Written By: Taylor Swift, Max Martin, and Shellback

Logically an electropop thumper with a dubstep breakdown shouldn’t have worked from a singer who unleashed “White Horse,” “Fifteen,” and “Mean” onto the world. But she piles on earworm appeal and turns the unexpected number into a rousing success. Singing along is rarely this much fun.

#22

Clean

1989 (2014)

Written By: Taylor Swift & Imogen Heap

Like “This Love,” “Clean” is an example of Swift’s smart lyrical side coming through the catchy pop of 1989. For those who say Swift’s changed, and I’ve been on of them, they need to give the new album a change. She hasn’t parted ways with her trademark songwriting – at least not yet.

#21

Back To December

Speak Now (2010)

Written By: Taylor Swift

Typical breakup ballads find the singer blaming the ex for the split while they come off bitter and jaded. But this relationship has Swift admitting fault, returning to that one fateful December where he did all he could to woo the emotional ice cube that routinely pushed him away. She’s regretful all right, but she knows the damage has already been done.

#20

Everything Has Changed (Featuring Ed Sheeran)

Red (2012)

Written By: Taylor Swift & Ed Sheeran

A sweet love song, and Swift’s first duet on one of her studio albums. She doesn’t need Sheeran to help bring this home, but his delicate touch only enhances the sentiment. Plus, it all led to one of the most adorable music videos in recent memory. Kudos for that.

#19

Tied Together With A Smile

Taylor Swift (2006)

Written By: Taylor Swift & Liz Rose

Sonically similar to “Tim McGraw,” this underrated ballad illustrated a sixteen-year-old wise far beyond her years. Swift’s observational prowess that has anchored her subsequent albums was fully formed from the onset, exemplified by a girl giving love away “like it’s extra change” only to leave her “like a penny in the rain.”

#18

Style

1989 (2014)

Written By: Taylor Swift, Max Martin, Shellback, and Ali Payami

Swift proves she doesn’t need subtly to craft an infectious lyric. “Style” is a play on her relationship with One Direction bandmate Harry Styles, from his slicked back hair and white t-shirt to her love of red lipstick. On the surface it sounds superficial, but the end result is so perfectly bouncy and happy, that it doesn’t even matter. “Style” is simply a great song and another Swift classic.

#17

Red

Red (2012)

Written By: Taylor Swift

Swift does an incredible job of keeping the romanticism of her music front and center, going as far as to keep the back-and-fourth she had with Scott Borchetta over this tune out of any official conversation. Swift and producer Nathan Chapman were at odds with Borchetta over production – he hated everything they came up with – until they finally settled on a magical banjo driven uptempo arrangement that perfectly matches the story comparing emotions to the colors of the rainbow.

#16

This Love

1989 (2014)

Written By: Taylor Swift

When asked, Swift has said this Nathan Chapman produced breathy ballad is her favorite number on 1989. Not surprisingly, it’s also the album’s sole nod to her country past. If this had appeared on Red it would’ve been loaded with fiddle and mandolin. How I would kill to here the country remix this track practically begs for. Not like it isn’t elegant and sophisticated in its current form.

#15

Change

Fearless (2008)

Written By: Taylor Swift

Written about the night Swift won the final CMA Horizon Award, “Change” is about the revolution when the walls came down and the biggest recording artist in the world took her almighty throne. In lesser hands this would be self-absorbed narcissism, but Swift instead turns it into an advancement anthem for the ages. She knows there’s “change” in all of us, if we just push through and discover it for ourselves.

#14

The Best Day

Fearless (2008)

Written By: Taylor Swift

At her core, Swift is a folk singer who happened to aspire to the muscle Scott Borchetta could bring to her music. This tribute to her mother was a surprise to her, presented in video form to the elder Swift for the first time. Like the George Strait hit before it, “The Best Day” is a perfect portrait of a child-parent relationship, built around the simple observances occurring throughout life.

#13

Mean

Speak Now (2010)

Written By: Taylor Swift

What’s one to do when they’re blasted for their inability to sing on pitch? Write a wickedly clever song that attacks the accusations head on. Like “Blank Space,” Swift turns the tables on herself. She also comes out with her most country sounding song in four years.

#12

You’re Not Sorry

Fearless (2008)

Written By: Taylor Swift

I always play Carrie Underwood’s “I Know You Won’t” immediately after playing this. Why? Both songs capture female angst in the face of a boy who just won’t call while showing off the best attributes of the artist delivering the lyric.

#11

Ours

Speak Now (2010)

Written By: Taylor Swift

Regulated to the deluxe edition of Speak Now, Big Machine had the good fortune to release it as a single. A female’s spin on Alan Jackson’s “Livin’ On Love” (already a male’s take on Tanya Tucker’s “Two Sparrows In A Hurricane”) with Swift declaring, “The stakes are high, the water’s rough, but this love is ours.”

#10

Dear John

Speak Now (2010)

Written By: Taylor Swift

Staying classy doesn’t always mean taking a high road as Swift beautifully demonstrates in the ultimate diss of John Mayer and his plundering ways. Allegedly inspired by a run-in at the 2010 CMT Video Music Awards, “Dear John” takes Mayer to task but not without Swift admitting her own faults – “I’ll look back in regret how I ignored when they said, “Run as fast as you can.”

#9

Innocent

Speak Now (2010)

Written By: Taylor Swift

Conventional wisdom says “Enchanted” is the masterpiece from Speak Now. I see it differently. In four years I haven’t been able to let go of “Innocent,” the wispy ballad serving as her last word in the Kanye West VMA debacle. Swift takes a high road that shouldn’t even exist, letting West off too easy – “It’s okay, life is a tough crowd, 32 and still growing up now. Who you are is not what you did, you’re still an innocent.” There’s a virtue in staying classy, and composing a kiss ass song in the process, but West’s actions will always be a dick move, no matter what.

#8

Fifteen

Fearless (2008)

Written By: Taylor Swift

Swift’s masterpiece on the psyche of high school from the perspective of romance and sex. Most young artists strive to write beyond their years, suppressing their age in an effort to appeal to everyone. Swift is the rare exception who did just that while unleashing her teenage perspective.

#7

Our Song

Taylor Swift (2006)

Written By: Taylor Swift

A talent show entry about a romance without an anthem became Swift’s first uptempo single, chart topper, and the moment I became obsessed. Not since Lila McCann and “I Wanna Fall In Love” nine years earlier had teenage exuberance been captured so wonderfully.

#6

Blank Space

1989 (2014)

Written By: Taylor Swift, Max Martin, and Shellback

Lonely Starbucks lovers aside, this slice of electropop is notable for Swift’s ability to turn the tables on herself and craft a lyric around the media’s relentless perception of her. This time it’s her role as a serial dater. Boys may only want love if it’s torture, but it’s Swift who’s the nightmare dressed as a daydream.

#5

Ronan

Ronan – Single (2012)

Written By: Taylor Swift and Maya Thompson

Easily Swift’s most heartbreaking composition, “Ronan” was written for a boy, who died from cancer and performed just once, on the 2012 Stand Up To Cancer television special. The lyric isn’t as fully formed as “All To Well” or “Dear John,” but Swift perfectly captures Thompson’s grief over her son’s untimely passing.

These types of songs are often heavy handed and weighted down by brazen emotional manipulation. But Swift handles the subject matter with a grace and maturity far surpassing her then 21 years. In the wake of “We Are Never, Ever Getting Back Together,” which she debuted not even a month prior, this was the welcomed return to form that arose through unthinkable tragedy. That she could write and sing a first person narrative this personal, that she didn’t live, is the remarkable feat that pushes “Ronan” over the top.

#4

Begin Again

Red (2012)

Written By: Taylor Swift

Swift has anchored her career writing about all facets of love, so it was only natural she’d pen a tune about the blossoming of a new relationship. But instead of reverting back to her tired cliché of fairytales and prince charming, she’s meeting her new man “on a Wednesday in a café” where they bond over James Taylor records, Christmas movies, and the past finally being behind them for good.

#3

White Horse

Fearless (2008)

Written By: Taylor Swift & Liz Rose

I’ve always wondered if the boy begging for forgiveness at Swift’s feet in “Should’ve Said No” was the same individual down on his knees begging for forgiveness here. How could it not be? Swift enjoys playing with her audience, turning her life into the ultimate guessing game. “White Horse” appeared during her fairytale days, a period when everyone was prince charming and she was their long-lost princess. But Swift was smarter than that, turning that image on its head, until the next boy came around.

#2

Tim McGraw

Taylor Swift (2006)

Written By: Taylor Swift & Liz Rose

Swift’s debut single is still one of her strongest records, eight years after its release. Effortlessly perfect, the dobro and fiddle flourishes flawlessly frame her vocal, which is a master class in innocence. Truly remarkable, though, is the fully-formed story – a young adult “Strawberry Wine” (minus the sex) that name-checks a 90s legend without pandering to any specific audience. Not since Dixie Chicks’ Home has an organic ballad sounded this good.

#1

All Too Well

Red (2012)

Written By: Taylor Swift & Liz Rose

“All To Well” is finest recording of Swift’s career to date. Her ability to craft a story stuffed with impeccably crafted details is astonishing. Her observances on childhood (“Just a little kid with glasses in a twin sized bed”) are as clever as those about weather (“After plaid shirt days and nights when you made me your own”). The bombastic climax (“You call me up again just to break me like a promise, so casually cool in the name of being honest”) drives it home, at which point you’re spent, and feeling Swift’s heartbreak right along with her.